47-year-old virgins, cross-dressing and parents’ sex lives

Dear Dan: I was involved with a straight man who enjoys cross-dressing and taking explicit photos. The problem is that the props he uses belong to his three children, all under age 12. For example, he dressed up as a slutty schoolgirl and wore his daughter’s backpack. He dressed up as a slutty cowgirl and posed with his son’s stuffed horse. He even had the horse eating his “carrot.” I told him he should not use his children’s things as props. He believes that his children will never see the photos, so no harm will come of it. I’m horrified at the thought of these kids (perhaps as adults) stumbling over these pictures. He posts them on Instagram and Facebook, so they aren’t private and he can’t control where they go. It’s one of the reasons I ended the relationship. Is there anything I can say to him?

—Canceled Definitely Promising Relationship Over Photo Sessions

Dear CDPROPS: You told him what he’s doing is wrong, you explained the enormous risk he’s running, and you dumped him, CDPROPS. You could take one last run at it and try to explain that his children finding these photos isn’t one of those “low-risk, high-consequence events,” i.e., something that’s unlikely to happen but would be utterly disastrous if it did. (Think of the super volcano that is Yellowstone National Park erupting or a deranged, racist billionaire somehow managing to win a U.S. presidential election.) Nope, if he’s posting these photos online, at least one of his children will stumble over them — or one of their friends will. (“Hey, isn’t this your dad? And your backpack?”) Your ex needs to knock this shit off, and will most likely need the help of a mental-health pro in order to do so.

Dear Dan: My parents were married for almost 40 years — and on paper, things seemed fine. They rarely fought and were an example of a strong, monogamous marriage until the day my mother died. Recently, I found writings by my dad revealing he had several casual encounters with men over the course of their marriage. Do I tell him I know? We are close, but sex isn’t something we usually discuss. What should I do with this information, if anything?

—A Deeply Upsetting Lie That Scalds

Dear ADULTS: When you say their relationship seemed fine “on paper,” ADULTS, what you mean is their relationship was decent and loving. Well, now you know it wasn’t perfect — but no relationship is. Your mother is dead (I’m sorry for your loss), and either she made peace with this fact about her husband long ago or she never knew about it. Either way, no good will come from confronting your father about the handful of dicks he sucked decades ago.

Dear WAH: There are lots of 40-year-old-and-up women out there who are virgins — they write in, too — so putting “middle-aged virgin seeks same” in your personal ad wouldn’t be a bad idea. Find someone in your same situation, WAH, and treat her with kindness, gentleness and patience — the same as you would like to be treated.

Dear Dan:I’m married and poly, with one partner in addition to my husband. My partner has a friend-with-benefits arrangement with a woman he’s been with since before we met. The FWB is not poly, but she’s always known my partner is. She has always insisted they’re not a couple, but he knows she would be hurt if she found out he was with someone else, so he has avoided telling her he’s now also with me. I don’t like being someone’s secret. My husband knows I’m with someone else and is fine with it. If my partner’s FWB felt the same, I wouldn’t see a problem. But this feels oddly like I’m helping my partner cheat on his FWB, even though they’re “not a couple” (her words). So it’s not cheating… is it?

—Pretty Obviously Lost, Yeah

Dear POLY: It’s not cheating — it’s plausible deniability. Your partner’s FWB would rather not know he’s seeing anyone else, so she doesn’t ask him about his other partners and he doesn’t tell. Accommodating his FWB’s desire not to know about other partners — doing the DADT open thing — does mean keeping you a secret, POLY, at least from her. If you’re not comfortable with that, you’ll have to end things with your partner.